Kelsey Reeves' Custom Caption Prize

Kelsey wanted a caption "about Britney Valentine where she is caught shoving a dildo up her ass and her pathetic dad walks in."

TheSickness's Custom Caption Prize

TheSickness wanted a caption where Nikki is humiliated in a public bathroom by Malik. Enjoy.

eXtreme's Custom Caption Prize

For his custom caption, eXtreme wanted me to caption a picture of this model with the storyline of a sissy who is seduced away from his white "boyfriend."

Megan Gwynn's Custom Caption Prize

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Slutty Eve's Custom Caption Prize

Eve wanted a caption of this particular photo and wanted me to take it in whatever direction I wanted. I decided to go the obvious (but fun) route.

Missy Sissy's Custom Caption Prize

For Missy's custom cap she asked for me to use this photo to make a father/son caption. I definitely took it in a dirty direction.

Public Punishment

Gym Partners

A Little Extra Money

Minor Compromises

Rooftop Battle

So Close, Yet So Far

Prom Threesome

First Aid

Role Models

Photo Evidence

Let's Get Physicals...Physicals

Bois Night Out

Quality Time With Stepdaddy

Surprises

Body Shop

I'm still waiting to hear back from TheSickness and eXtreme about their custom captions. If you two read this, check your email and get back to me.

Substitute Instructor

Dad's Helper

Surprise Party

My apologies to Megan Gwynn and TheSickness. I screwed up my post on the winner's page for the winners of the Prison Sissy Caption Contest. I mistakenly attributed TheSickness's caption to Megan and completely forgot to post Megan's caption. All fixed now. No more mixing bourbon and sissy captions for me.

Number One Fan